


Natural Progression

by JackTrades



Series: I Like To Watch [3]
Category: Supernatural
Genre: Anal Sex, Dirty Talk, F/F, F/M, Filthy, Multi, Oral Sex, PWP, Plot What Plot/Porn Without Plot, Rough Sex, Threesome, Threesome - F/M/M, Wincest - Freeform
Language: English
Status: Completed
Published: 2015-08-14
Updated: 2015-08-14
Packaged: 2018-04-14 17:48:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,170
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4573968
Author URL: https://archiveofourown.org/users/JackTrades/pseuds/JackTrades
Summary: <blockquote class="userstuff">
              <p>Upon hearing that one of Dean's recent hookups wanted to have a threesome, Sam wonders why they haven't tried that.</p><p>Can be read as a standalone or as part of the series.</p>
            </blockquote>





	Natural Progression

**Author's Note:**

> You can read this as a standalone or as part of the series. If you're reading this as a standalone, the only smut background you need to know is that one brother jerked off while the other had sex with a girl in front of him. Twice "recently" to the events in this story.

Sam sometimes asked and sometimes didn't… Hearing Dean laughing to himself when Sam was zoned out, staring out the window during a long drive, that wasn't an uncommon occurrence. Dean was always cracking himself up. Their relationship made them comfortable with long periods of silence. Something about that chuckle got Sam's attention though, "What's up?"

"Huh?" Apparently Dean didn’t realize that he was making noise at all.

"You were just laughing to yourself." Sam was going to give him the opportunity to share before making fun of how dorky Dean could be.

"Nothing, I was just thinking about that girl I boned in front of you..." Sam rolled his eyes.  Of course he was thinking about sex. "She was almost disappointed that I wasn't propositioning her for a threesome..."

"What?!" Dean had been holding out on him!

"I didn't tell you that?" Dean was genuine with that response.

"No!" Sam's morbid curiosity wouldn't let him leave it alone previously.  Dean had accounted what happened leading up to the night he brought a girl to the room for Sam to watch him with before.  He thought he knew all the details.

"Yeah, well, that happened." Dean was cracking himself up now, as Sam sat there stupefied.

 The thought had occurred to him in the past.  Heck, it occurred to him when Dean showed up with that particularly memorable 'birthday present.’  Now he started over thinking it again… Unfortunately for Sam, he had one thought out loud, "Well, would you?"

"Would I, what?" Dean’s eyebrow twitched at the question but he didn't want to jump to conclusions.

Sam squirmed a little bit.  This was one of those no return conversations. "...Have a threesome?"

Dean rolled his eyes, "I've had my share of them, Sam. They're not all they're cracked up to be."

"So have I, jerk, but-"

"What! When?" Right.  Secrets.  Sam still had a few.

"Uhhh college," he couldn't temper the sarcasm if he tried.

"Tsk tsk, you were holding out on me!" Dean raised an eyebrow completely this time, "You gonna give details?"

"Are you?"

"I asked first..."

They get points for maturity.  Neither budged at first. Sam cracked though, "Junior year," he leaned further into the window, "Jess and I had been on a break and I kinda took out my frustrations by fucking everyone that was willing..."

"So slutty, Sammy," Dean laughed.

"Do you want me to tell you or not?"

"Sorry," he was still laughing.

"Soooooooo I went with my friend Brady to some mixer. I got completely trashed and went home with two girls from Delta Zeta."

"And?"

"And, what?" Sam was always stingy on the details.

"Good? Bad? Indifferent?"

"Overwhelming, I guess," he paused to gather his thoughts, "You know more of them and it's difficult to get one off without the other one trying to blow you or something... I mean it's really unfair that girls' orgasms just get them more fired up! I mean it’s great to be the center of attention.  I just didn’t wanna be the loser to blow, like, thirty seconds into it.  I guess it was a better idea in theory…"

Dean had to burst out laughing, "Guys are just as bad." Then had his 'oh shit' moment realizing he hadn't really disclosed everything he'd done either.

"Oh?" Dean's freak out didn't go unnoticed and Sam was not letting him off the hook.  Dean was all about women.  Dean was all about titties and pussy and wouldn’t hesitate to share his enthusiasm about both, whether Sam wanted to hear it or not. Guys though? Sam wasn’t aware of any guys.

Dean gave a heavy sigh. "Ok, I'll agree about the girls thing.  I hooked up with twins. It was weird... and yeah..." He clearly his throat and continued, "So like I said, I had a few tangos.  And when you went away to school, and dad and I were doing separate cases, I would do some wild stuff.  Whatever, I wanted to try everything because you never know until you try.  I had this case where a spirit was targeting people at a tavern, turned out to be straightforward.  Old owner, maybe two or three prior, had passed away and had an attachment to the place. Came back after he was dead. Totally routine and boring case – not that I’m complaining – and the main owner that had called in for help was grateful, extremely grateful, and so was his boyfriend... Their ‘Let me thank you’ dinner was not exactly a meal.  I mean, whatever, I was 24 and they were offering something I hadn't tried before..." Sam was legitimately shocked.  His brother not only had sex with a guy, but two guys, at the same time. His brain was working overtime and he realized he wasn’t even listening to Dean. "... I mean, at the end of the day I just really like pussy too much. A couple asked me on a job once too but they chickened out on me.  It stopped short after a few minutes making out.  Dude didn't like his girl moaning on me. I was bummed too! I really wanted to try double penetration.  Still do, but you know, not like our lifestyle allows for that.  Just got to hope for an opportunity and not blow it."

Sam processed this information silently before piping up again, "But you didn't answer my question."

"Would I do it? I have done it, twice, totally answered!"

"No, I mean would you..." Sam should really stop because now he's walking a dangerous line, "You know? With me. I mean, shit, we've already seen each other fucking. It seems like the natural progression of this... this thing we’ve been doing."

"Natural progression?"

"You know what I mean!"

"Are you propositioning me?" Dean had to make him squirm some more. 

And Sam did squirm. Then he tried to backtrack, obviously he misread this and he didn't need Dean thinking Sam had other intentions. Nope, certainly no other intentions there! "Look, you're not into it. I get it..."

"The fuck, I'm not into it! Sam, yes, if you were into it and we met someone who was consenting and into both of us... I'd definitely give it a go.  With some boundaries of course."

"Boundaries? What is this a negotiation?" Sam’s relief was giving way to busting Dean’s chops right back.

“You brought it up, dickbag!”

“Hey don’t be so sensitive, Dean! You’re saying you have deal breakers? Because that’s kind of shocking to me.  Based on all your damn stories it sounds like you’ve yet to try something that you didn’t like – save for a threesome with two gay guys appearently –“

“Fuck you.  First off, that threesome was awesome.  I just like how girl feel, you know –“

“Not really.  You could just be with a fat dude and it’s basically the same…”

Dean couldn’t help the shit-eating grin that he got, “So I guess you were a gay chubby chaser in college too? We’re learning so much about each other!”

“Fuck you.  No.  And don’t change the subject! What boundaries?”

“Well first off, you already fucking know I don’t like that you’re so damn rough with girls when you fuck them.” Sam nodded in acknowledgement.  “I’m not asking you to ratchet it back, but if we were gonna do it together I would not be down for that manhandling and hair pulling shit you pull.”

“Yeah, because your slow shit is so much better –“

“Excuse me?! It’s called being sensual, Sam!”

“Okay, ‘sensual.’ Your ‘sensuality’ is fucking boring and I wouldn’t be down for it if we were to hypothetically do this.

 

* * *

 

The terms broke down pretty fairly: if they were to find a girl, she definitely got to call all the shots.  No touching each other's junk, even if the girl asked for it.  Spit roasting was fine, but not preferable.  Sam would have to cut back on the roughness and Dean would have to cut down on the slow teasing. Various positions were discussed, but inevitably looped back to 'whatever the girl wants.'  If given the options, Dean wanted to go down on her and Sam preferred anal sex.  Not much that they didn't already know about each other, because their lives didn't offer much in the way of privacy.

* * *

 

That should have been it.  It should have stayed hypothetical. But no.  It ended up here, in a dingy motel with a woman who was more than willing.  Holy hell, was she into it? She tried to pick Sam up by grabbing his ass while he was hustling at darts.  When Dean came over to see if he needed rescuing, the rest kind of became a blur.

This was seven shades of fucked up.  How did they even get here? Why did he let this escalate so quickly? Sam’s choice of moments to mentally freak out just happened well after the point of no return… Now he was wearing only his boxers while sitting up against the headboard. His legs were splayed wide and wrapped over hers, keeping her wide open for Dean.  Dean wasn't kidding about his enthusiasm for vagina. Sam had seen him going to town before, but not from this angle.  The girl was leaning back against Sam, panting and writhing.  Sam had one arm locked around her waist and the other alternated between rubbing up and down her arm and playing with her breasts.  Sam was getting off on restraining her while Dean put his mouth to good use. That’s when Sam’s brain decided to pull the emergency brake and have the ‘this has gone too far’ meltdown. At least it was until Dean flicked his eyes up to meet the girl’s gaze, which happened to also be in Sam’s general direction.  The unbridled lust and dripping promise of sex in his eyes, shit, the girl looked like she’d come just from that look and Sam wasn’t fairing much better himself. He was suddenly telling his rational part of the brain going ‘dirty’ / ‘wrong’ / ‘disgusting’ to fuck itself in favor of seeing if that wicked gaze lived up to its clearly conveyed promises.

She was very close based on the clenching of her thigh muscles and the increasing volume of her noises.  Dean definitely had at least two fingers in her pussy as he alternated between flicking his tongue over her clit and sucking it hard. It even started to look puffy at this point, Sam still unsure if it was normal arousal or if Dean was purposely sucking it hard enough to make that happen. Dean would let out a stray moan here and there, exactly like he did when he was popping a boner about how good food was.  Good luck not associating food with sex forever after this, Sam.

Dean was feeling particularly merciless tonight, and didn't pull back once she tipped over the edge.  Her second chased the first one pretty quickly, Dean using a trick he’d picked up in some porn.  He had just rubbed hard over her G-spot while pressing hard on her clit, not moving that hand, it had a decent success rate when he did it. Dean was taking a gamble that this girl was multi-orgasmic and wouldn’t push him away from the overstimulation. She screamed when she came that time.  Sam laughed and tried to muffle her with a hand but that was not very effective.   The room phone was ringing shortly after that.

Sam reached over to take the call, knowing exactly how that conversation would go.  Dean was laughing but trying to muffle it to the best of his ability. “Yes. Yes we understand. Yep, we’ll keep it down. Bye.” Not the first time either of them had that call either.  Fuck the neighbors.  This already escalated to this point, so what if they got kicked out of the motel when they were done?

Sam hung up the phone and went back to the bed. He approached their new friend and tapped her shoulder to encouraged her to lean forward.   It was time to rearrange their collective position. He moved her so she was on her hands and knees. Dean was still between her legs for the most part, lying on his back and still trying to lap at her pussy before Sam tapped him on the chin, "My turn." Sam ended up straddling Dean to get between her legs.  He had lube in hand and was coating his fingers when Dean ran a hand up Sam's leg.  Ok, this was the thing he had not thought about in advance. He knew Dean had a kink for being sensual and running his hands all over his partners... but now he was that partner! He couldn’t stop the breathy gasp that he let out. Dean chuckled in response, nipping at the girl's leg while Sam traced the rim of her ass. Sam's dick was definitely leaking and it was because of what Dean was doing, he was going to have to work that out in his head later. Sam was going to be efficient about prepping her because Dean knew too many of Sam's triggers and he wouldn't be surprised if Dean used that knowledge to make him bust a nut unnecessarily early.  Dean slid his hands up to cup Sam's ass before firmly kneading the muscles there. Two could play that game. As Sam used one hand to scissor his fingers in the woman, he reached down with the other hand to start toying with Dean’s nipple. He started softly circling, teasing around it before firmly pinching it. Dean let out a heavy moan and arched into the touch. Sam decided he didn’t care for how much range of motion Dean had and sat further down on him, proud when Dean keened as he continued his teasing.

When Sam felt she was thoroughly prepped, he pulled out and asked her, "How did you want to do this?"

She looked over her shoulder, already looking debauched, "What?"

Dean stopped his own movements to listen. Sam clarified, "How do you want us? Like, what positions?"

"Oh god," she dropped her glaze and blushed profusely. "I wanna ride you while he is on top of me."

Sam jumped off the bed to discard his boxer briefs, his cock slapping against his stomach with an audible 'thwap' as he did that. He rolled on a condom and got on the bed, leaning back on the headboard. She mounted him reverse cowgirl style and positioned herself over his cock. Sam was holding himself steady as Dean gripped her hips, encouraging her to sink down onto Sam. All three moaned at the welcome insertion; Dean was enamored watching Sam's large cock disappear into her. "Sammy. You're stretching her so good. Bet you I can barely get my cock in 'cause she's so filled out right now."

Rather than following instructions, Dean leaned over and began to flick his tongue over her clit again, and thrust two fingers inside her. She clench around Sam from that, and Dean moaned again, "Give me a hand, Sammy. You gotta feel yourself inside her right now." It was true. Dean's fingers were pushing against her walls to feel the ridge of Sam's cock as he spoke.  Sam was happy to oblige, god, Dean might actually be the death of him if this is how this is going to go.  Dean guided Sam’s hand in and kept one of his own in too. The girl was gushing in almost no time, between Sam's upward thrusts and Dean rubbing her clit and both fingering her. They didn't give her time to recover, Dean then pushed into her and it was an extremely tight fit, just as he suspected.  Sam watched Dean’s face as he rubbed his hands up and down her flanks to gauge if this was too much for her.  Seeing Dean like this up close was ridiculously hot. Without thinking about the consequences, Sam grabbed the back of Dean’s head and pulled him into a rough, harsh, sloppy kiss over the girl's shoulder.  Dean yanked back out of it then bit Sam's lower lip hard.  Hard enough to draw blood.  Then he leaned back in to lick over the fresh split and blood.  Dean growled, definitely not a moan, it was hard, dominant, animalistic shit that almost sent Sam over the edge.  Sam didn’t have a minute to process this development though, because Dean began thrusting roughly. Sam was going to let him do the work for now, because he was holding the girl steady and wasn’t exactly confident he could thrust and have parts of himself touching parts of Dean without coming right this second.  Dean almost felt bad for this girl.  Now that he had himself in her, and could feel Sam everywhere on and around him, he was going to wreck her just to get to Sam.  When Sam finally composed himself, he began to thrust but at a completely different pace than Dean.  He was going to have to work with Dean if they didn’t want to just have this woman between them topple over.

Dean didn’t know it at the time, but Sam's one careless move awoke some primal instinct in him.  The girl between them was trying to cling to anything that would keep her grounded.  Eventually settling on Dean’s shoulder and the bed sheets.  Dean’s rough thrusts eventually synced with Sam's and the air was filled with the sounds of grunts, moans, panting, and the slap of skin on skin.  Sam wanted more leverage and spoke up with as much cohesiveness as he could muster, "De-Dean, wanna switch positions..."

Dean pulled out and yanked the girl from Sam at the same time.  Sam took the opportunity to push Dean so he was sprawl on his back then encouraged the girl to straddle him.  Now it was Sam's turn to groan as he watched his brother's cock plunging in and out of her. Sam put an authoritative hand on her back and pushed her forward until she was lying flush with Dean. He kept the hand there as he slid into her again.

Dean didn’t need to reach down to flick his fingers over her clit, but he absolutely knew that he could get this girl to tap out from orgasm overload if he did.  She arched as much as she could while being sandwiched between them. Sam was thrusting hard, she ended up grabbing the wall and the nightstand in an attempt to push back and get something resembling leverage.  Dean was trying to keep pace but was now in the position of holding her up and back so that she didn’t, literally, get fucked through the wall by Sam.  Her eyes were rolled back into her skull and it looks like she had temporarily forgotten how to breathe. Time to go in for the kill, Dean pressed his mouth close to her ear and let his filthy words take over. "You have enough yet? Look at you. Can you even understand the words coming out of my mouth right now? No? You're just a fuckdoll for us right now. Some holes for us to tear up..."

Sam faltered, he could hear Dean too, "Shut the fuck up, Dean." He tried to compose himself.

Dean never was good at taking mercy once Sam indicated that he had gotten under his skin. "What's wrong, Sammy?" He purposely made eye contact and held it.  A mix of challenge, danger, and unbridled lust was what Sam saw in Dean’s eyes. "You were doing so good and you want me to stop talking. You worried that I'll say something to offend our friend? No.  That's not it... you're worried I will be able to talk you off, right?" Sam's eyes gave him a warning look. "Yeah, that's it. You don't want to nut off before we're done.  Once we get this fucktoy to give up I'm fucking you senseless.  And you only have yourself to blame, Sammy, because you started this shit."

It was certainly effective.  The woman was coming hard after that shameless, unfiltered display.  Luckily for all of them, Dean was much better at muffling her cries than Sam was. Sam was fucking her through it and clearly not going to last much longer.  Dean kept his hand over her mouth and his other arm locked around her waist.  He was thrusting as effectively as he could in this position.  He was ready for this to end, the woman on top of him clearly wasn’t going to last much longer, he took action.  “Come on Sammy, come for us.  Please.  You’re doing so great – I wanna see how hot you look when you come from this angle.  Come on.” Sam was already holding on by a thread.  Dean’s fucked up hybrid of begging and praise was already a lot. So when Dean moved his hand from the woman’s mouth to rub reassuringly on Sam’s forearm with a final, “Come on Sammy,” in that desperate sounding voice… Sam came hard.

Sam threw his head back as he gave one final thrust as deep as he could get, one hand digging into Dean’s arm and the other gripping the woman’s hip hard enough to leave a bruise.  Dean wasn’t disappointed, Sam looked gorgeous like that. He was stunned though with a shout of, “DEAN!” escaping Sam’s mouth when Sam came.  For better or worse, that’s now permanently etched into Dean’s memory.  Sam made a move to pull away when Dean grabbed his arm.  He pulled Sam downward towards him, not particularly caring if he was crushing the woman between them at the moment.  Dean moved his other arm from her waist to the back of Sam’s neck, lacing his fingers through the sweat soaked hair on Sam’s head. He encouraged Sam to bring his head down so his forehead was flush with Dean’s.  Dean stared directly into Sam’s eyes as he resumed his thrusting, panting breath and lust-filled eyes washing over Sam. All Sam could do was whimper in response, it was overwhelming.  Dean didn’t last much longer, overwhelmed himself, and Sam got a front row seat to seeing Dean’s face as he came. 

They lay there for a few moments before Dean finally spoke up, “You’re crushing me, Sasquatch.” Sam took that as his cue to roll off the both of them.  The woman between them had, in fact, been fucked senseless because she looked completely checked out with glassed over eyes.  Dean got up and grabbed a bottle of water for her.  She took it but was clearly still sex stunned.  Sam had gone back to his bed and was already almost passed out.  They did agree that Dean would drive her back to her car at the bar when this was over. He rummaged through the room to find his clothes before approaching Sam on the bed, “Need anything?” An unintelligible grunt and Sam rolling onto his side was response. Guess that’s a no. Certainly a crazy night, to say the least.

When he returned, Dean managed to get back into the room without disturbing Sam and probably slept better than he had in years. Even though he was exhausted, he still put up their routine level of protection in the room.  When he woke, Sam had already gone to get breakfast and coffee.  Not a bad thing to wake up to.  Sam, for his part, was typing on his laptop with a bag of ice pressed to his lip.

"Oh jeez, sorry man," Dean’s sleep rough voice conveyed his sincerity. 

"You didn't have to bite me," Sam said as he put the cold pack back to his lower lip.

"I got carried away. And I'm sorry, maybe we should -"

"Do it again?" Sam interjected with his eyebrow raised and wore an expression between challenge and negotiation.

"What like with just each other?" Dean was taken aback but the question was out before his filter could stop it.

"What? No! No, that's not what I meant - "

"Good, because our lives are fucked up enough as it is!"

"- and dad would kill us."

"Dude. If he knew half the shit we've already done, he'd kick our asses at the very least!" Dean let go of the breath he didn’t realize he was holding and Sam carefully studied him before speaking up again.

"I'm just saying, watching sometimes is fun. Last night was awesome even if we took it a little far..." Dean was curious where Sam was going with this. "The more, uhhh... active... participation was great. I definitely wouldn't have seen you look that hot from the other bed or across the room in a chair."

"And you probably learned a thing or two, bitch," Dean’s cocky swagger was back in full force as he started drinking his coffee.

Sam rolled his eyes, "Tell yourself whatever you need to, jerk."

Dean barked out a laugh, "Pack your bag, Sammy. We've got to hit the road in 20 minutes."

**Author's Note:**

> As always comments and kudos make Jack happy.
> 
> Sadly I had two gifs that inspired this one and one of those is no longer around. Part of the inspiration was this porn gif found here http://yessssboss.tumblr.com/post/126308421549  
> 


End file.
